Cut the Low-Hanging Fruit. Stack the Moves That Win the Future.

Apr 29, 2025

A series on building long-term strategy that holds up - even when the pressure’s on.

This is the first essay in a series on long-term thinking, at a time when short-termism is winning. Pressure is high. Budgets are tight. Everyone’s judged on what they shipped, sold, or saved - this quarter. Bosses and boards confuse “future” with next week’s deliverables. So we chase what’s fast. What’s visible. What we can explain in the next meeting without getting side-eyed. But this is exactly when long-term thinking matters most. When it’s harder to hold, and more valuable to practice. The only way to actually be alive when the real future hits.

More essays coming soon.

Strategy That Stacks

Why the low-hanging fruit is rotting your strategy and how to fix it.

The pressure’s real.
Teams are lean. Resources are frozen. Leaders are being asked one thing, again and again:

“What’s going to pay off right now?”

And under that kind of heat, long-term thinking is often the first thing to go.

When every move has to justify itself this quarter, strategy gets reduced to what’s easy to explain and quick to execute:

The low-hanging fruit
The short-term win
The slide that looks strategic but doesn’t stack

Low-hanging fruit doesn’t just stall your strategy. It actively rots it from within.

Chasing easy wins creates the illusion of progress, but underneath, it drains focus, wastes resources, and corrodes long-term advantage. Every disconnected success story is another crack in the foundation.

It feels good in the moment because it rewards speed, visibility, and approval - all the signals we’re trained to chase. But it’s strategic self-sabotage: trading durable value for a sugar rush of activity.

Left unchecked, low-hanging fruit doesn’t just delay real progress. It corrupts orientation completely, leaving teams busier, louder, and marching confidently in the wrong direction.

Busy doesn’t win. Stacking wins.

Think of the team that launches five new features in five months, all with solid metrics, but no shared story, no cumulative advantage. They’re productive. But they’re not building power.

Real Strategy Stacks

Great strategists don’t just make smart decisions.
They build sequences - where each move sets up the next, and momentum begins to compound.

Stacking is the art of sequencing strategic decisions so each one amplifies the next: Creating momentum that builds, instead of resets.

It’s not about chasing bold bets or sketching radical visions.
It’s about making every step smarter because of the one before it, until the vision becomes inevitable.

But here’s where it gets misunderstood:

Stacking is not a linear project plan.
It’s not just slicing a big idea into smaller tasks and calling it a roadmap.
And no: faster sprints on your favorite Agile board don’t guarantee strategic depth.

In fact, sometimes Agile is the antidote to stacking, because it prioritizes velocity over sequencing, and iteration over accumulation.

Stacking is nonlinear.
It’s architectural.
It’s about earning leverage through intentional design, not just execution.

And this applies beyond product or brand.
Stacking plays out in org design, business models, capital allocation, and hiring.
The right structure at the right time can set up three future moves before anyone sees them coming.

Beyoncé Didn’t Just Reinvent, She Stacked

Let’s break it down (and yes, this one’s for Lisa - dear friend and Beyoncé lover):

🎤 She launched a global tour
→ Not just for ticket sales, but to generate energy, content, and cultural saturation.

🎥 Turned the tour into a documentary
→ A second medium. A broader audience. A deeper narrative.

💣 Dropped it without promo
→ Owned the moment. Controlled the message. Hijacked the media cycle.

👑 Used the attention
→ To push Ivy Park, drive streaming numbers, and expand her creative independence.

Each move wasn’t just successful.
It made the next move more powerful.
That’s stacking.

And no, it didn’t follow a project plan.
It followed a strategic rhythm, one only visible in hindsight.

Strategy That Stacks: 5 Questions That Actually Matter

When timelines are tight and the stakes are high, use these questions to cut through the noise:

1. Does this move play to my strengths or dilute them?
Strategic moves generate energy. If a decision pulls you away from your edge, it might deliver output, but not impact.

2. Does this increase my surface area for leverage or shrink it?
Not all wins open doors. Some lock you into maintenance. Stacking moves widen your path forward.

3. What becomes easier - or cheaper - because of this?
Real strategy reduces future friction: time, cost, resistance, complexity. If a move doesn’t lighten the next step, it’s just motion.

4. Would this still matter if I looked back from five years out?
Would you point to this with pride or forget it happened by next quarter?

5. Is the added value obvious and sharp enough to shift power?
If it doesn’t create energy at the top, it won’t create movement at the bottom. Strategy needs clarity that travels.

And what blocks stacking isn’t just bad plans: it’s misaligned incentives, impatient loops, and “good” metrics that don’t lead anywhere.

TL;DR

If your short-term wins don’t compound, they’re distractions.
If your long-term plan doesn’t sequence leverage, it’s just wishful thinking.

Smart strategy doesn’t reward the most motion.
It rewards the best sequence.

Because anyone can make a good move.
The real skill is making the next move better because of this one.

🔐 Want the full framework?

Paying subscribers get access to the extended breakdown:
Stacking Strategy – How to design moves that compound strategic value, even under pressure.

Inside:
• The 5 types of leverage moves that expand future options
• How to sequence across business model, narrative, and org focus
• A clear way to tell when you’re building momentum or just treading water

→ Drops in 2 weeks.
→ Beyoncé would approve. Lisa already does.